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    Amino acid derivatives, their production and use in preparing carbapenem and carbapenam compounds
    3.
    发明授权
    Amino acid derivatives, their production and use in preparing carbapenem and carbapenam compounds 失效
    氨基酸衍生物及其在制备碳水化合物和碳水化合物中的生产和使用

    公开(公告)号：US5118831A

    公开(公告)日：1992-06-02

    申请号：US661246

    申请日：1991-02-27

    申请人： Shigeo Nozoe ,  Tomihisa Ohta

    发明人： Shigeo Nozoe ,  Tomihisa Ohta

    IPC分类号： C07D477/00 ,  C07C67/00 ,  C07C239/00 ,  C07C271/08 ,  C07C271/22 ,  C07D207/16 ,  C07D477/04

    CPC分类号： C07C271/22 ,  C07D207/16 ,  C07D477/04 ,  Y02P20/55

    摘要： Novel amino acid derivatives of the formula ##STR1## wherein R.sup.1 is a protecting group removable under reducing or acid conditions, and R.sup.2 and R.sup.5 are hydrogen or carboxylic protecting groups, are useful as intermediates in preparing stereospecific carbapenam/carbapenem derivatives. R.sup.1 is removed under reducing conditions to form a pyrrolidine derivative, which is further cyclized from the R.sup.5 .dbd.H compound to form a .beta.-lactam ring. Stereospecificity at the 6-position is achieved by treatment with lithium diisopropylamide (LDA) and quenching at different temperatures. Compound (I) can be prepared by treating R.sup.1 -protected R.sup.3 -pyrrolidone carboxylic acid R.sup.2 -ester with a lithium enolate of the formula R.sup.4 CHLiCO.sub.2 R.sup.5. The lithium enolate can be formed from R.sup.4 CH.sub.2 CO.sub.2 R.sup.5 by treatment with LDA.

    Optically active pyrrolidine derivative
    4.
    发明授权
    Optically active pyrrolidine derivative 失效
    光学活性吡咯烷衍生物

    公开(公告)号：US5342963A

    公开(公告)日：1994-08-30

    申请号：US915808

    申请日：1992-09-15

    申请人： Kuniya Sakurai ,  Kunisuke Izawa ,  Hiroyuki Izawa ,  Takashi Ineyama ,  Tomihisa Ohta ,  Shigeo Nozoe

    发明人： Kuniya Sakurai ,  Kunisuke Izawa ,  Hiroyuki Izawa ,  Takashi Ineyama ,  Tomihisa Ohta ,  Shigeo Nozoe

    IPC分类号： C07D207/16 ,  C07D401/06 ,  C07D477/02 ,  C07D477/04 ,  C07D477/14 ,  C07D477/20 ,  C07D207/00 ,  C07D401/00 ,  C07D405/00 ,  C07D487/00

    CPC分类号： C07D477/20 ,  C07D207/16 ,  C07D401/06 ,  C07D477/02 ,  C07D477/04 ,  C07D477/14 ,  Y02P20/55

    摘要： Optically active pyrrolidine derivative represented by the following formula (XI): ##STR1## wherein R.sup.1 represents a benzyl group R.sup.2 represents an alkyl group having 1 to 6 carbon atoms, R.sup.3 represents an alkyl group having 1 to 6 carbon atoms, a benzyl group or an allyl group, R.sup.4 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may be substituted with a protected hydroxyl group, a vinyl group, a phenyl group which may be substituted, a benzyl group which may be substituted, and a heterocyclic ring having 1 to 4 nitrogen or/and oxygen atoms, and R.sup.5 represents a hydrogen atom or a methyl group.This compound can be an intermediate for synthesis of carbapenem antibiotic compounds.

    摘要翻译： PCT No.PCT / JP91 / 01619 Sec。 371日期：1992年9月15日 102（e）日期1992年9月15日PCT 1991年11月26日PCT PCT。 出版物WO92 / 09605 日期：6月11日，1992。下式（XI）表示的视觉活性吡咯烷衍生物：其中R1表示苄基R2表示碳原子数1〜6的烷基，R3表示具有 1至6个碳原子，苄基或烯丙基，R 4选自氢原子，可被被保护的羟基取代的具有1至6个碳原子的烷基，乙烯基， 可以被取代的苯基，可以被取代的苄基，以及具有1〜4个氮原子或/或氧原子的杂环，R 5表示氢原子或甲基。 该化合物可以是合成碳青霉烯类抗生素化合物的中间体。

    Amino acid derivatives, their production and use in preparing carbapenem and carbapenam compounds
    5.
    发明授权
    Amino acid derivatives, their production and use in preparing carbapenem and carbapenam compounds 失效
    氨基酸衍生物，其制备和用于制备碳青霉烯类和碳青霉烯类化合物

    公开(公告)号：US5028718A

    公开(公告)日：1991-07-02

    申请号：US360534

    申请日：1989-06-02

    申请人： Shigeo Nozoe ,  Tomihisa Ohta

    发明人： Shigeo Nozoe ,  Tomihisa Ohta

    IPC分类号： C07D477/00 ,  C07C67/00 ,  C07C239/00 ,  C07C271/08 ,  C07C271/22 ,  C07D207/16 ,  C07D477/04

    CPC分类号： C07C271/22 ,  C07D207/16 ,  C07D477/04 ,  Y02P20/55

    摘要： Novel amino acid derivatives of the formula ##STR1## wherein R.sup.1 is a protecting group removable under reducing or acid conditions, and R.sup.2 and R.sup.5 are hydrogen or carboxylic protecting groups, are useful as intermediates in preparing stereospecific carbapenam/carbapenem derivatives. R.sup.1 is removed under reducing conditions to form a pyrrolidine derivative, which is further cyclized from the R.sup.5 .dbd.H compound to form a .beta.-lactam ring. Stereospecificity at the 6-position is achieved by treatment with lithium diisopropylamide (LDA) and quenching at different temperatures. Compound (I) can be prepared by treating R.sup.1 -protected R.sup.3 -pyrrolidone carboxylic acid R.sup.2 -ester with a lithium enolate of the formula R.sup.4 CHLiCO.sub.2 R.sup.5. The lithium enolate can be formed from R.sup.4 CH.sub.2 CO.sub.2 R.sup.5 by treatment with LDA.

    Process for preparing carbapenem compounds
    6.
    发明授权
    Process for preparing carbapenem compounds 失效
    碳青霉烯化合物的制备方法

    公开(公告)号：US5204459A

    公开(公告)日：1993-04-20

    申请号：US853069

    申请日：1992-03-17

    申请人： Shigeo Nozoe ,  Tomihisa Ohta

    发明人： Shigeo Nozoe ,  Tomihisa Ohta

    IPC分类号： C07C271/22 ,  C07D207/16 ,  C07D477/04

    CPC分类号： C07C271/22 ,  C07D207/16 ,  C07D477/04 ,  Y02P20/55

    摘要： Novel amino acid derivatives of the formula ##STR1## wherein R.sup.1 is a protecting group removable under reducing or acid conditions, and R.sup.2 and R.sup.5 are hydrogen or carboxylic protecting groups, are useful as intermediates in preparing stereospecific carbapenam/carbapenem derivatives. R.sup.1 is removed under reducing conditions to form a pyrrolidine derivative, which is further cyclized from the R.sup.5 =H compound to form a .beta.-lactam ring. Stereospecificity at the 6-position is achieved by treatment with lithium diisopropylamide (LDA) and quenching at different temperatures. Compound (I) can be prepared by treating R.sup.1 -protected R.sup.3 -pyrrolidone carboxylic acid R.sup.2 -ester with a lithium enolate of the formula R.sup.4 CHLiCO.sub.2 R.sup.5. The lithium enolate can be formed from R.sup.4 CH.sub.2 CO.sub.2 R.sup.5 by treatment with LDA.

    摘要翻译： 式IMA的新型氨基酸衍生物，其中R 1是在还原或酸性条件下可除去的保护基，R 2和R 5是氢或羧基保护基，可用作制备立体特异性碳青霉烯/碳青霉烯衍生物的中间体。 在还原条件下除去R1以形成吡咯烷衍生物，其进一步从R5 = H化合物环化形成β-内酰胺环。 通过用二异丙基氨基锂（LDA）处理和在不同温度下淬火来实现6位的立体定向性。 化合物（I）可以通过用式R4CHLiCO2R5的烯醇化锂处理R1保护的R3-吡咯烷酮羧酸R2-酯来制备。 烯醇化锂可以通过用LDA处理从R4CH2CO2R5形成。

    Amino acid derivatives, their production and use in preparing carbapenem and carbapenam compounds
    7.
    发明授权
    Amino acid derivatives, their production and use in preparing carbapenem and carbapenam compounds 失效
    氨基酸衍生物，其制备和用于制备碳青霉烯类和碳青霉烯类化合物

    公开(公告)号：US4876383A

    公开(公告)日：1989-10-24

    申请号：US95445

    申请日：1987-09-11

    申请人： Shigeo Nozoe ,  Tomihisa Ohta

    发明人： Shigeo Nozoe ,  Tomihisa Ohta

    IPC分类号： C07D477/00 ,  C07C67/00 ,  C07C239/00 ,  C07C271/08 ,  C07C271/22 ,  C07D207/16 ,  C07D477/04

    CPC分类号： C07C271/22 ,  C07D207/16 ,  C07D477/04 ,  Y02P20/55

    摘要： Novel amino acid derivatives of the formula ##STR1## wherein R.sup.1 is a protecting group removable under reducing or acid conditions, and R.sup.2 and R.sup.5 are hydrogen or carboxylic protecting groups, are useful as intermediates in preparing stereospecific carbapenam/carbapenem derivatives. R.sup.1 is removed under reducing conditions to form a pyrrolidine derivative, which is further cyclized from the R.sup.5 .dbd.H compound to form a .beta.-lactam ring. Stereospecificity at the 6-position is achieved by treatment with lithium diisopropylamide (LDA) and quenching at different termperatures. Compound (I) can be prepared by treating R.sup.1 -protected R.sup.3 -pyrrolidone carboxylic acid R.sup.2 -ester with a lithium enolate of the formula R.sup.4 CHLiCO.sub.2 R.sup.5. The lithium enolate can be formed from R.sup.4 CH.sub.2 CO.sub.2 R.sup.5 by treatment with LDA.

    摘要翻译： 式IMA的新型氨基酸衍生物，其中R 1是在还原或酸性条件下可除去的保护基，R2和R5是氢或羧基保护基，可用作制备立体特异性碳青霉烯/碳青霉烯衍生物的中间体。 在还原条件下除去R1以形成吡咯烷衍生物，其进一步从R5 = H化合物环化形成β-内酰胺环。 通过用二异丙基氨基锂（LDA）处理并在不同温度下淬火来实现6位的立体定向性。 化合物（I）可以通过用式R4CHLiCO2R5的烯醇化锂处理R1-保护的R3-吡咯烷酮羧酸R2-酯来制备。 烯醇化锂可以通过用LDA处理从R4CH2CO2R5形成。